Homes for Sale near Dutchess Day School

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  /35

  $1,400,000

  • 3 Beds
  • 8 Baths
  • 10,689 Sq Ft

  4258 Route 44, Millbrook, NY 12545

  This distinctive property in the heart of Dutchess County combines historic character with over 10,000 square feet of versatile residential and commercial potential. Originally built in the 19th century as a Congregational church, the building has enjoyed a rich history and now offers endless possibilities for its next chapter. The expansive main level features multiple gathering areas, soaring

  Stephen Pener William Pitt Sothebys Int Rlty

  4258 Route 44, Millbrook, NY 12545
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  Explore Dutchess Day School

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  /26

  $1,295,000

  • 3 Beds
  • 2.5 Baths
  • 2,237 Sq Ft

  44 Merrit Ave, Millbrook, NY 12545

  A rare village offering on one of Millbrook’s prettiest streets, this beautifully updated three-story Victorian blends timeless character with thoughtful modern upgrades, The main residence features Three bedrooms and 2.5 baths across three spacious light-filled levels, with hardwood floors throughout and classic architectural details that reflect the home’s historic roots. The welcoming living

  OLIVER BROWN Houlihan Lawrence Inc.

  44 Merrit Ave, Millbrook, NY 12545
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  /40

  $1,069,000

  • 4 Beds
  • 3.5 Baths
  • 3,001 Sq Ft

  45 Maple Hill Dr, Millbrook, NY 12545

  Introducing the first home in Hidden Glen, Millbrook's Newest Luxury Community, featuring eight custom residences set on gorgeous one+ acre, level tree-lined homesites. This Millbrook Design offers 3,001 square feet of expertly crafted living space, featuring custom design and upscale finishes throughout. Located within the highly regarded Millbrook School District, this elegant new construction

  TINA TOWNSEND BHHS Hudson Valley Properties

  45 Maple Hill Dr, Millbrook, NY 12545
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  /50

  $1,800,000

  • 7 Beds
  • 7 Baths
  • 11,222 Sq Ft

  3893 Route 82, Millbrook, NY 12545

  Set on 11.1 private acres in the heart of Millbrook, this stately brick Colonial estate offers over 11,222 square feet of refined living space, combining timeless elegance with exceptional versatility. A true legacy property, it delivers the scale, design, and amenities expected by the most discerning buyers.A dramatic two-story granite foyer welcomes you with a sweeping double staircase and

  Howard Payson RE/MAX Town & Country

  3893 Route 82, Millbrook, NY 12545
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  /39

  $1,895,000

  • 4 Beds
  • 3 Baths
  • 3,488 Sq Ft

  425 Camby Rd, Verbank, NY 12585

  When beauty, history, tradition, and ease intersect in one lovely home, it’s 425 Camby Road. Located minutes to the Village of Millbrook on 20 private acres including two barns, two ponds, manicured and landscaped lawns, sweeping meadows, and walking paths. Classic New England charm dates back to the mid-1800s with 21st century updates, this center hall colonial conveys the warmth of generations

  Candy Anderson Compass Greater NY, LLC

  425 Camby Rd, Verbank, NY 12585
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  /37

  $1,395,000

  • 4 Beds
  • 3 Baths
  • 3,068 Sq Ft

  3311 Franklin Ave, Millbrook, NY 12545

  A Rare Village Gem in the Heart of Millbrook Don’t miss this exceptional opportunity to own a beautifully maintained and thoughtfully updated home on a spacious 0.21-acre lot in the heart of the charming Village of Millbrook. Perfectly positioned just steps from shops, restaurants, and local galleries, this 2,132+ sq. ft. residence blends historic character with modern comfort. Originally built

  Ann Stettner Neil Charles Real Estate, LLC

  3311 Franklin Ave, Millbrook, NY 12545
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  /26

  $1,950,000

  • 3 Beds
  • 1 Bath
  • 1,482 Sq Ft

  21-23 Tinker Town Rd, Dover Plains, NY 12522

  A few minutes east of Route 22 on the Dover/Millbrook border in the municipality of Washington, sits 109+ acres of picturesque countryside. Used prior as a dairy farm, this exceptional offering presents a rare opportunity to bring your farming lifestyle dreams to life, or an equestrian property. Comprised of 4 distinct parcels totaling 109+ acres, the property blends open fields, wooded

  Brian McGrath McGrath Realty Inc

  21-23 Tinker Town Rd, Dover Plains, NY 12522
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  /8

  $1,250,000

  • 4 Beds
  • 3.5 Baths
  • 3,196 Sq Ft

  43 Maple Hill Dr, Millbrook, NY 12545

  New home under construction featuring a primary bedroom on the first level, high-end finishes, and exceptional attention to detail throughout. A two-story foyer with arched entry welcomes you to the formal living room, dining room, and the seamlessly connected kitchen and family room. Beautiful white oak flooring spans the entire first level, and the thoughtfully designed layout provides the

  TINA TOWNSEND BHHS Hudson Valley Properties

  43 Maple Hill Dr, Millbrook, NY 12545
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  /9

  $995,000

  • Land
  • 23.49 Acres
  • $42,358 per Acre

  Parcel 1 - TBD Woodstock Rd, Millbrook, NY 12545

  Located just outside the Village of Millbrook on a scenic gravel country road, Old Oaks Woods is a 23.49-acre parcel offering a picturesque setting for your dream retreat. The land features a mix of old-growth forest and walking trails, bordered by charming stone walls and highlighted by a pair of peaceful ponds. A large barn and chicken coop remain on the property. Build your private weekend

  OLIVER BROWN Houlihan Lawrence Inc.

  Parcel 1 - TBD Woodstock Rd, Millbrook, NY 12545
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  /34

  $299,000

  • 5 Beds
  • 2 Baths
  • 2,100 Sq Ft

  14-16 Glen Hill, Dover Plains, NY 12522

  Surrounded by nature. An affordable multifamily compound in the quiet hamlet of Dover Plains—an increasingly rare opportunity to own two homes for the price of one. This unique property features a 3-bedroom/1-bath residence and a separate 2-bedroom/1-bath home, both in solid condition with some TLC needed to make them your own. Set on a picturesque parcel at the end of a country road, the setting

  Barry Malawer Coldwell Banker Realty

  14-16 Glen Hill, Dover Plains, NY 12522
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  /23

  $675,000

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft

  3875 Route 82, Millbrook, NY 12545

  Exceptionally well maintained home with many upgrades including new siding, newer roof, new hard-wired generator, new windows, new flooring on first level, newly paved driveway.Private first level includes bedroom, full eat in kitchen, living room, full bath, laundry room and separate entrance. It's the perfect for extended family living.Upstairs includes full, eat in kitchen, dining

  Valerie Foster K. Fortuna Realty, Inc.

  3875 Route 82, Millbrook, NY 12545
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  /31

  $895,000

  • 4 Beds
  • 3.5 Baths
  • 3,136 Sq Ft

  35 Appaloosa Ln, Millbrook, NY 12545

  Perfectly situated at the end of a long driveway and enjoying complete privacy is this four bedroom Ranch on 8.94 +/- acres offering a picturesque setting and located only minutes to the Village of Millbrook. The lovely interior features an open floor plan with many fine details throughout such as Anderson windows, custom trim and hardwood floors. The spacious open country Kitchen is fully

  Carey Whalen Compass Greater NY, LLC

  35 Appaloosa Ln, Millbrook, NY 12545
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  /9

  $1,050,000

  • Land
  • 28.43 Acres
  • $36,933 per Acre

  TBD Woodstock Rd, Millbrook, NY 12545

  Quiet Meadow South – A rare offering of 28.43 acres of open land at the corner of Stanford Road and Woodstock Road. Bucolic field, a corner pond, and distant views create a stunning backdrop for a future homestead or agricultural endeavor. Located just outside the Village of Millbrook, this scenic parcel offers easy access with the feel of wide-open countryside. Additional land available.

  OLIVER BROWN Houlihan Lawrence Inc.

  TBD Woodstock Rd, Millbrook, NY 12545
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  /33

  $650,000

  • 3 Beds
  • 3 Baths
  • 1,914 Sq Ft

  33 Upper Ln, Millbrook, NY 12545

  Millbrook Hollow is a wonderful condominium complex on acres of natural beauty in a tranquil setting. With a total of 18 units, this distinctive, serene residential neighborhood is located off the main avenue in the Village of Millbrook, just a short stroll to all Village amenities. This inviting end unit offers a delightful sun-lit interior and the stunning wood floors grace the elegant dining

  Susan Whalen George T Whalen Real Estate

  33 Upper Ln, Millbrook, NY 12545
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  /3

  $79,000

  • Land
  • 1.49 Acres
  • $53,020 per Acre

  0 Tinker Town Rd, Dover Plains, NY 12522

  Escape the NYC and come to see THIS MIX USE 1.49 acre lot in Amenia, NY. Nestled in the beautiful Dutchess County, this level plot offers endless possibilities for those looking to build a custom home or business or both. This property provides a canvas for your dreams . A Natural Haven Just Minutes from Modern Conveniences, The lots proximity to the Taconic State Parkway and the Dover Plains

  Adnane Chahi Keller Williams Realty Partner

  0 Tinker Town Rd, Dover Plains, NY 12522
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  /19

  $159,000

  • Land
  • 5.1 Acres
  • $31,176 per Acre

  565 Halls Corners Rd, Dover Plains, NY 12522

  Builder's Dream... A lot was Completed on this Property, survey, well, electric, foundation started, driveway started and more. Build your DREAMHOME on this Beautiful Magnificent Property with BOHA 5.1 acre lot. Many Permits are Completed. Well/ Septic and plans are Board of HealthApproved for a 3 Bedroom home, valid thru July 2027. Completed projects include: Survey. 1+ acre building

  Helen Sclafani World Homes Realty

  565 Halls Corners Rd, Dover Plains, NY 12522
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  /23

  $195,000

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  110 Gina Dr, Dover Plains, NY 12522

  Beautifully maintained and absolutely gorgeous double manufactured home offering spacious open-concept living in the desirable Tally Ho 55+ community. This home features a large living room with a cozy electric fireplace and a gourmet kitchen loaded with extras, including refrigerator, dishwasher, microwave, propane stove, abundant cabinetry, and a breakfast island perfect for casual dining and

  Robert Dunlop Havens Real Estate

  110 Gina Dr, Dover Plains, NY 12522
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  /50

  $799,000

  • 3 Beds
  • 2.5 Baths
  • 2,284 Sq Ft

  568 Oak Summit Rd, Millbrook, NY 12545

  Millbrook Modern Log Retreat sited on Nearly 3.5 Secluded Acres. Set quietly amid rolling landscape and enveloped by nature, this exquisitely restored log residence offers a rare blend of rustic authenticity and modern refinement. Perched on a knoll, the home unfolds as a serene escape—thoughtfully reimagined to deliver both comfort and understated luxury. From the moment you enter, the interiors

  Nicole Porter

  568 Oak Summit Rd, Millbrook, NY 12545
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  /50

  $5,500,000

  • 4 Beds
  • 5.5 Baths
  • 6,244 Sq Ft

  3585 Route 82, Millbrook, NY 12545

  Welcome to Sunset Ridge Farm. A discreet tree-lined drive with expansive views of two aerated ponds and rolling hills leads to this breathtaking modern farmhouse estate. Set on 10 exquisitely manicured acres with mountain vistas, a heated in-ground pool, spa, and gardens reminiscent of the English countryside, 3585 Route 82 is a truly rare offering — a perfect full-time residence or refined

  Jordan Vaccaro Serhant LLC

  3585 Route 82, Millbrook, NY 12545
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  /41

  $929,000

  • 3 Beds
  • 3 Baths
  • 2,033 Sq Ft

  611 N Clove Rd, Millbrook, NY 12545

  Mid Century Modern. Tucked quietly among the trees on 9 private acres, this striking contemporary retreat—known as The Treehouse—offers a rare blend of architectural distinction and natural serenity, overlooking a peaceful swimming pond with its own dock. Designed in 1973 by Richard Stein around a 1950’s cottage, the home showcases a bold sawtooth roofline and clerestory windows that flood the

  PAULA REDMOND Corcoran Country Living

  611 N Clove Rd, Millbrook, NY 12545
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  /6

  $944,900

  • 4 Beds
  • 2.5 Baths
  • 2,829 Sq Ft

  37 Maple Hill Dr, Millbrook, NY 12545

  This to-be-built Mayfair style home will be located in Hidden Glen, Millbrook's newest Luxury Community, featuring eight custom residences set on gorgeous one+ acre, level, tree-lined homesites. This popular design offers 2,829 square feet of beautifully crafted living space and upscale finishes throughout. A grand two-story entry foyer leads to an open kitchen and breakfast area overlooking the

  TINA TOWNSEND BHHS Hudson Valley Properties

  37 Maple Hill Dr, Millbrook, NY 12545
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  /21

  $7,900,000

  • Land
  • 441.99 Acres
  • $17,874 per Acre

  1297 New York 343, Dover Plains, NY 12522

  Nestled in the heart of natural beauty, this extraordinary property offers over 440 acres of pristine land in the municipality of Washington. A rare find, this expansive tract of land is a harmonious blend of rolling hay fields, lush pastures, mature hardwood forests, three tranquil ponds and meandering stream. The property rises from east to west, providing breathtaking views across the Harlem

  Brian McGrath McGrath Realty Inc

  1297 New York 343, Dover Plains, NY 12522
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  /6

  $954,000

  • 3 Beds
  • 2 Baths
  • 2,030 Sq Ft

  66 County House Rd, Millbrook, NY 12545

  To Be Built. Introducing Millbrook's newest luxury community, Hidden Glen at Millbrook, offering eight custom residences set on gorgeous one+ acre, level tree-lined homesites. The Rochester ranch-style home is positioned on a premium lot and offers 2,030 square feet of convenient one-level living. The foyer opens to a dramatic family room with volume ceilings, flowing seamlessly into the kitchen

  Brian Mossey BHHS Hudson Valley Properties

  66 County House Rd, Millbrook, NY 12545
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  /40

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  89 Deer Pond Rd, Verbank, NY 12585

  Privately situated on 4 acres and at the end of a quiet cul-de-sac, find this custom contemporary. Complete with stocked pond, inground pool & massive three bay barn, this unique property will surely impress. Attractive floor plan features kitchen w/sunroom annex overlooking the expansive backyard. Living room w/fireplace flows seamlessly to secondary sunroom & family room w/bar. Huge first floor

  Dan Axtmann BHHS Hudson Valley Properties

  89 Deer Pond Rd, Verbank, NY 12585
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  /31

  $65,000,000

  • 10 Beds
  • 8 Baths
  • 14,706 Sq Ft

  45 Hitchcock Ln, Millbrook, NY 12545

  The Hitchcock Estate is an exceptional property in size, location and history. The property has 2078 acres intact since the first owner assembled it from 5 area farms in 1889. Located in the heart of Millbrook, NY it has remained undeveloped, shrouded in mystique, the subject of curiosity and imagination providing now and then a glimpse into its elegant and storied past. Beginning as a summer

  HEATHER CRONER William Pitt Sothebys Int Rlty

  45 Hitchcock Ln, Millbrook, NY 12545
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  /11

  $190,000

  • Land
  • 1.66 Acres
  • $114,458 per Acre

  0 New York 22, Dover Plains, NY 12522

  Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522
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  /25

  $800,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  247 N Mabbettsville Rd, Millbrook, NY 12545

  Set on a landscaped acre just minutes from the Village of Millbrook, this cottage offers a comfortable, well-planned layout with a sense of privacy and ease. The main level is bright and welcoming, with wood floors throughout and a living room centered around a gas fireplace. Windows bring in natural light and views of the surrounding lawn, giving the space a relaxed, connected feel.The

  Jill Rose Houlihan Lawrence Inc.

  247 N Mabbettsville Rd, Millbrook, NY 12545
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  /21

  $529,000

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  256 Hammond Hill Rd, Dover Plains, NY 12522

  Privately nestled on 3 serene acres in the rolling hills of Dover Plains, this beautifully reimagined country retreat offers an exceptional blend of privacy, refined modern updates, and effortless indoor-outdoor living. Set far back from the road and surrounded by mature trees and picturesque natural scenery, 256 Hammond Hill Road delivers a peaceful lifestyle with extraordinary entertaining

  Anna Proctor Compass Greater NY, LLC

  256 Hammond Hill Rd, Dover Plains, NY 12522
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  /19

  $359,000

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  81 Verbank Rd, Millbrook, NY 12545

  Welcome to 81 Verbank Road, a mid-century colonial set on nearly an acre in a peaceful country setting, just minutes from the Village of Millbrook. This charming home offers great potential, indoor and outdoor living space, and a flexible layout. Enjoy morning coffee on the covered front porch or relax on the covered rear deck overlooking the property. The main entrance opens to a generously

  Dave Longbard KW MidHudson

  81 Verbank Rd, Millbrook, NY 12545
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  /3

  $450,000

  • 5 Beds
  • 3 Baths
  • 3,318 Sq Ft

  37 Glen Ave, Dover Plains, NY 12522

  2 homes for the price of 1. This is a multi-family property on multiple structures. Two separate electrical meters. 3318 total sq ft with a flowing stream in backyard. Main house consists of 3 bedrooms and 2 baths. Bungalow house has 2 bedrooms and 1 bath. 1 hr to NYC. INVESTORS AND CONTRACTORS SPECIAL. Needs Renovation.

  Ishwar Rameshar YourHomeSold Guaranteed Realty

  37 Glen Ave, Dover Plains, NY 12522
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  /39

  $499,000

  • 2 Beds
  • 2 Baths
  • 1,598 Sq Ft

  121 Stanford Rd, Millbrook, NY 12545

  Here is a rare opportunity to acquire a slice of Millbrook history. The original Millbrook Toll House Circa 1890, built alongside the Wappingers Creek at the Arch Bridge is a true gem. The Toll House has been lovingly restored, preserved, and maintained, with an utmost respect for its grace, integrity and historical significance. Exposed beams/hardwood pristine, whimsical nooks and crannies

  Terese Mondello MONDELLO UPSTATE PROPERTIES LLC

  121 Stanford Rd, Millbrook, NY 12545
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  /2

  $100,000

  • Land
  • 36,154 Sq Ft
  • $120,482 per Acre

  9 Terbar Ct, Dover Plains, NY 12522

  Beautiful flat building lot, no clearing needed! Board of health approved for 4 bedroom home and you only need a small septic on this lot which makes building a home here more cost effective! This level lot is perfect to build your dream home. Bring your own builder or use ours! We can help and assist the first time homebuyer build their dream home through the whole process.

  Bliss Voutsinas Hillside Realty & Development

  9 Terbar Ct, Dover Plains, NY 12522
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  /45

  $900,000

  • 4 Beds
  • 6.5 Baths
  • 5,050 Sq Ft

  3534 Route 82, Millbrook, NY 12545

  Discover a truly unique Millbrook estate set on over 6 acres with a private pond, fruit trees, and beautiful natural surroundings. This expansive stone and brick residence offers remarkable craftsmanship and imported finishes, including marble and other materials brought in directly from Italy. Designed for both elegance and comfort, the home features multiple kitchens, two formal dining rooms,

  Christian Baez Keller Williams Hudson Valley

  3534 Route 82, Millbrook, NY 12545
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  /11

  $205,000

  • Land
  • 2.5 Acres
  • $82,000 per Acre

  0 New York 22, Dover Plains, NY 12522

  Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522
• 

  

  /11

  $195,000

  • Land
  • 1.85 Acres
  • $105,405 per Acre

  0 New York 22, Dover Plains, NY 12522

  Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522
• 

  

  /18

  $599,408

  • 4 Beds
  • 2 Baths
  • 2,148 Sq Ft

  810 New York 343, Dover Plains, NY 12522

  Set on 2.1 serene acres in the heart of Dutchess County, this thoughtfully designed 4-bedroom, 2-bath residence offers a harmonious blend of classic charm and modern functionality. Ideally positioned near the Wassaic Train, the Taconic Parkway, Millbrook, and Dover Plains, the property provides both privacy and convenience. Step inside to discover warm wood floors throughout the main level,

  Arleen Shepley Elyse Harney Real Estate

  810 New York 343, Dover Plains, NY 12522
• 

  

  /18

  $599,408

  • 4 Beds
  • 2 Baths
  • 2,148 Sq Ft

  810 Route 343, Dover Plains, NY 12522

  Sophisticated country living in the desirable Millbrook area within the highly regarded Millbrook Central School District. Ideally located close to the charming village, local amenities, and the Wassaic Station for convenient Metro-North access to New York City. Privately set on 2.06 picturesque acres, this light-filled 4-bedroom, 2-bath Cape offers the perfect blend of comfort, versatility, and

  Arleen Shepley Elyse Harney Real Estate

  810 Route 343, Dover Plains, NY 12522
• 

  

  /25

  $750,000

  • 2 Beds
  • 2 Baths
  • 1,540 Sq Ft

  1 Johnson Ln, Millbrook, NY 12545

  Originally built as the gatehouse to the Standish estate, this charming vernacular cottage dates to 1895 and is defined by its gabled roofline and storybook proportions. Set on a two acre parcel tucked among neighboring estates, the property is enveloped by old-growth trees, established gardens, and open meadow. Just minutes from the village of Millbrook, the home feels wonderfully private --

  Annabel Taylor Four Seasons Sotheby's Int.

  1 Johnson Ln, Millbrook, NY 12545
• 

  

  /11

  $799,000

  • 3 Beds
  • 2.5 Baths
  • 2,426 Sq Ft

  477 Canoe Hill Rd, Millbrook, NY 12545

  Early Country Cottage on 5 acres on a quiet country road in Millbrook, 5 minutes from the village. An excellent fishing stream borders the property. 3 bedrooms, 2 ½ bathrooms. Wood burning fireplaces in kitchen, living room and dining room. Barns. Property offered "As Is"

  HEATHER CRONER William Pitt Sothebys Int Rlty

  477 Canoe Hill Rd, Millbrook, NY 12545
• 

  

  /43

  $2,600,000

  • 3 Beds
  • 6 Baths
  • 2,614 Sq Ft

  188 Nine Partners Ln, Millbrook, NY 12545

  This 1800’s Millbrook farmhouse has been totally renovated to today’s buyers wishes and needs featuring an open floor plan for the kitchen and dining area with three sets of French doors opening to a porch and the new outdoor kitchen pavilion and pool house equipped with kitchen facilities and powder room. A light filled three season sunporch with fireplace offers views of the meadow. The formal

  ANN WILKINSON Compass Greater NY, LLC

  188 Nine Partners Ln, Millbrook, NY 12545

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